Nassim Taleb: "I was effectively short volatility. [...] I would have been harmed by small movements. I was set up to be harmed by small movement and gain if the move continues to something very large." [1]
He also described in one of his books that this strategy works because on most days you will lose money, and most people psychologically don't like that. But you have to ignore that and keep betting until you suddenly make a lot of money.
In case you don't know Taleb and would like to point out that he probably is a fraud, please note that his books and articles have been cited 39946 times according to Google Scholar. See also his Wikipedia [2]. Although I am aware that these are all popularity-based metrics, I unfortunately don't have a better metric available. I invite you to read his books for yourself and make your own decision on his credibility.
> I do buy slightly OTM options and it's barely profitable and even so I think mostly out of pure luck. No way would someone have done this trade without inside info.
Okay if the discussion is whether this particular trade was unlikely I can agree, but your "No way" makes no sense to me.
Taleb's point seems more to be that he saw a mispricing and traded on it one day, rather than anything profound regarding option pricing, unless I am missing something. Anyway, it has little to do with what's being said in the article.
Now that you say it could be that he misspoke indeed.
> Taleb's point seems more to be that he saw a mispricing and traded on it one day
Okay so Taleb was literally an "option trader" as in he traded one option on one day in his life?
> Anyway, it has little to do with what's being said in the article.
How is Taleb, who is an option trader and who has written about options trading for years, not related to an article on an options trade?
I should be clear that what you seem to think ties these together, i.e:
> given the volatility, at least one would be a hit in this month.
I don't actually believe to be true. It's not like these options aren't being priced somewhat accurately. There could be insanely high volatility and all that needs to happen is for the price to go up instead of down for none of your options to "hit."